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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 24
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Original Articles

First Total Synthesis of Bauerine C

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Pages 4313-4318 | Received 08 May 2007, Published online: 14 Dec 2007
 

Abstract

The first total synthesis of Bauerine C, a unique indoloquinazoline alkoloid, has been achieved from readily available 2,3‐dichloroaniline. The key step is the Japp–Klingmann condensation between 2,3‐dichloroaniline and ethyl‐2‐acetyl‐5‐phthalimido pentanoate to get 3‐[(2,3‐dichlorophenyl)‐hydrozono]‐pipiridin‐2‐one, which cyclizes to 7,8‐dichloro‐2,3,4,9‐tetrahydro‐β‐carbolin‐1‐one, which can be methylated by dimethyl sulphate to give 7,8‐dichloro‐9‐methyl 2,3,4,9‐tetrahydro‐β‐carbolin‐1‐one. This N‐methyl derivative is then subjected to dehydrogenation with 2,3‐dichloro‐5,6‐dicayano‐1,4‐benzoquinone (DDQ) to give the target compound Bauerine C.

Acknowledgment

The authors thank Dr. Reddy's Laboratories, Ltd., for supporting this work and Abhijit Mukherjee and Vilas Dahanukar of Custom Pharmaceutical Services for their constant help and encouragement. Cooperation extended by colleagues from the analytical division is gratefully acknowledged.

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